Sodium Methoxide → HCID 21876385, compound

HRID 858529Notes

Reaction equation

HRID 858529 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12]Cl.[CH3:14][O-:15].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH2:12][O:15][CH3:14]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 13640145HCID 13640145, compound

Product 1

HCID 21876385HCID 21876385, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1,5-dichloro-2-(chloromethyl)-4-nitrobenzene (Hagmann, William K.; Dorn, Conrad P.; Frankshun, Robert A.; O'Grady, Laura A.; Bailey, Philip J.; et al.; JMCMAR; J. Med. Chem.; EN; 29; 8; 1986; 1436–1441, 10.6 g, 44 mmol) in methanol (30 ml) was added sodium methoxide (44 ml, 66 mmol) at room temperature. The mixture was stirred at 80° C. for 21 h. The volatile component was removed under reduced pressure, and the residue was extracted with ethyl acetate (100 ml). The organic layer was washed with water (50 ml), brine (50 ml), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography eluting with hexane/ethyl acetate (6:1/4:1) to afford 2.8 g (27%) of the title compound as pale yellow oil.

Workup

  1. customThe volatile component was removed under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate (100 ml)
  3. washThe organic layer was washed with water (50 ml), brine (50 ml)
  4. dry with materialdried (Na2SO4)
  5. customAfter removal of solvent
  6. customthe crude product was purified by flash column chromatography
  7. washeluting with hexane/ethyl acetate (6:1/4:1)

Sources & evidence

ORD record
ord-584396a23c894ece80d836b91e06d131
Source dataset
uspto-grants-2006_12
Patent number
US07148234B2

Reaction notes

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